N-methyl-2-pyrrolidone → 6-chloropyrazine-2-carboxamide

HRID 1670668Notes

Reaction equation

HRID 1670668 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[N:4][CH:3]=1.C[N:12]1C(=O)CCC1.ClC(OCC(C)C)=O.[NH4+].[OH-]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH2:12])=[O:10])[CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 14923Ammonium HydroxideHCID 62365Isobutyl chloroformateHCID 145008756-Chloropyrazine-2-carboxylic acid

Product 1

HCID 12825296-chloropyrazine-2-carboxamideYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 6-chloro-pyrazine carboxylic acid (2.00 g, 12.62 mmol) in DMF (7 mL) was cooled to −40° C. NMP (2.77 mL, 25.23 mmol) and isobutyl chloroformate 3.27 mL, 25.23 mmol) were added. The temperature was allowed to increase to −20° C. during 20 min and then NH4OH was added. A precipitate was rapidly formed and after 15 min it was filtered off and washed with water. Crystallization from EtOH gave the title compound (670 mg, 34%) as light-brown needles.

Workup

  1. customA precipitate was rapidly formed and after 15 min it
  2. filtrationwas filtered off
  3. washwashed with water
  4. customCrystallization from EtOH

Sources & evidence

ORD record
ord-33ab6d8102cd4e9ea026058c8acacab9
Source dataset
uspto-grants-2011_08
Patent number
US07994179B2

Reaction notes

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